WO2006127205A3 - Methods of preparing 3-cyano-quinolines and intermediates made thereby - Google Patents

Methods of preparing 3-cyano-quinolines and intermediates made thereby Download PDF

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Publication number
WO2006127205A3
WO2006127205A3 PCT/US2006/016019 US2006016019W WO2006127205A3 WO 2006127205 A3 WO2006127205 A3 WO 2006127205A3 US 2006016019 W US2006016019 W US 2006016019W WO 2006127205 A3 WO2006127205 A3 WO 2006127205A3
Authority
WO
WIPO (PCT)
Prior art keywords
methods
preparing
quinolines
cyano
intermediates made
Prior art date
Application number
PCT/US2006/016019
Other languages
French (fr)
Other versions
WO2006127205A2 (en
Inventor
Warren Chew
Maria Papamichelakis
Original Assignee
Wyeth Corp
Warren Chew
Maria Papamichelakis
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wyeth Corp, Warren Chew, Maria Papamichelakis filed Critical Wyeth Corp
Priority to MX2007014773A priority Critical patent/MX2007014773A/en
Priority to EP06751635A priority patent/EP1883621A2/en
Priority to CA002608394A priority patent/CA2608394A1/en
Priority to AU2006249598A priority patent/AU2006249598A1/en
Priority to JP2008513497A priority patent/JP2008542267A/en
Priority to BRPI0610144-5A priority patent/BRPI0610144A2/en
Publication of WO2006127205A2 publication Critical patent/WO2006127205A2/en
Publication of WO2006127205A3 publication Critical patent/WO2006127205A3/en
Priority to NO20075643A priority patent/NO20075643L/en
Priority to IL187303A priority patent/IL187303A0/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/23—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same unsaturated acyclic carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/30—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same unsaturated acyclic carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/04—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers
    • C07C257/06—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers having carbon atoms of imino-carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms, or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings

Abstract

The present invention relates to methods for preparing substituted 3-cyanoquinolines and intermediates obtained by the methods of the present invention. The methods of the invention comprise reacting an N-aryl-2-propanimide with phosphoryl chloride to produce the substituted 3-cyanoquinolines. The methods further comprise reacting arylamines, orthoformates and active methylenes to produce the N-aryl-2-propenamide.
PCT/US2006/016019 2005-05-25 2006-04-27 Methods of preparing 3-cyano-quinolines and intermediates made thereby WO2006127205A2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
MX2007014773A MX2007014773A (en) 2005-05-25 2006-04-27 Methods of preparing 3-cyano-quinolines and intermediates made thereby.
EP06751635A EP1883621A2 (en) 2005-05-25 2006-04-27 Methods of preparing 3-cyano-quinolines and intermediates made thereby
CA002608394A CA2608394A1 (en) 2005-05-25 2006-04-27 Methods of preparing 3-cyano-quinolines and intermediates made thereby
AU2006249598A AU2006249598A1 (en) 2005-05-25 2006-04-27 Methods of preparing 3-cyano-quinolines and intermediates made thereby
JP2008513497A JP2008542267A (en) 2005-05-25 2006-04-27 Process for preparing 3-cyano-quinoline and intermediates produced thereby
BRPI0610144-5A BRPI0610144A2 (en) 2005-05-25 2006-04-27 method of preparing a substituted 3-cyanoquinoline; compound represented by formula i; and compound represented by formula ii
NO20075643A NO20075643L (en) 2005-05-25 2007-11-06 Methods for the preparation of 3-cyanoquinolines and thereby prepared intermediates
IL187303A IL187303A0 (en) 2005-05-25 2007-11-11 Methods of prepering 3 - cyano - quinolines and intermediates made thereby

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US68468305P 2005-05-25 2005-05-25
US60/684,683 2005-05-25

Publications (2)

Publication Number Publication Date
WO2006127205A2 WO2006127205A2 (en) 2006-11-30
WO2006127205A3 true WO2006127205A3 (en) 2007-05-10

Family

ID=36845416

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/016019 WO2006127205A2 (en) 2005-05-25 2006-04-27 Methods of preparing 3-cyano-quinolines and intermediates made thereby

Country Status (15)

Country Link
US (1) US20060270669A1 (en)
EP (1) EP1883621A2 (en)
JP (1) JP2008542267A (en)
KR (1) KR20080016600A (en)
CN (1) CN101180269A (en)
AU (1) AU2006249598A1 (en)
BR (1) BRPI0610144A2 (en)
CA (1) CA2608394A1 (en)
CR (1) CR9508A (en)
IL (1) IL187303A0 (en)
MX (1) MX2007014773A (en)
NO (1) NO20075643L (en)
RU (1) RU2007139544A (en)
WO (1) WO2006127205A2 (en)
ZA (1) ZA200710163B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2777675C2 (en) * 2017-10-18 2022-08-09 Цзянсу Хэнжуй Медисин Ко., Лтд. Method for production of tyrosine kinase inhibitor and its intermediate compound

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE602006021142D1 (en) 2005-02-03 2011-05-19 Gen Hospital Corp METHOD FOR THE TREATMENT OF GEFITINIB-RESISTANT CANCER
CN103110948A (en) 2005-11-04 2013-05-22 惠氏公司 Antineoplastic combinations with mTOR inhibitor,herceptin, and/or HKI-272
US8022216B2 (en) * 2007-10-17 2011-09-20 Wyeth Llc Maleate salts of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof
DK2656844T3 (en) 2008-06-17 2015-03-02 Wyeth Llc ANTINEOPLASTIC COMBINATIONS CONTAINING HKI-272 AND VINORELBINE
CN105963313A (en) 2008-08-04 2016-09-28 惠氏有限责任公司 Antineoplastic combinations of 4-anilino-3-cyanoquinolines and capecitabine
AU2010234968B2 (en) 2009-04-06 2015-05-14 Wyeth Llc Treatment regimen utilizing neratinib for breast cancer
CN106074445B (en) * 2009-11-09 2018-12-21 惠氏有限责任公司 The purposes of the drug of illness is eliminated or is reduced in coated drugs orbicule and its preparation
CN102649778A (en) * 2011-02-23 2012-08-29 苏州波锐生物医药科技有限公司 Quinazoline derivative and purposes thereof in preparing antineoplastic drugs
CN102718749A (en) * 2011-03-30 2012-10-10 北京德众万全药物技术开发有限公司 Preparation method of antitumor drug Nuonatini
WO2014127214A1 (en) 2013-02-15 2014-08-21 Kala Pharmaceuticals, Inc. Therapeutic compounds and uses thereof
US9688688B2 (en) 2013-02-20 2017-06-27 Kala Pharmaceuticals, Inc. Crystalline forms of 4-((4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-yl)oxy)-1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)butan-1-one and uses thereof
ES2831625T3 (en) 2013-02-20 2021-06-09 Kala Pharmaceuticals Inc Therapeutic compounds and their uses
JP6426194B2 (en) 2013-11-01 2018-11-21 カラ ファーマシューティカルズ インコーポレイテッド Crystalline forms of therapeutic compounds and uses thereof
US9890173B2 (en) 2013-11-01 2018-02-13 Kala Pharmaceuticals, Inc. Crystalline forms of therapeutic compounds and uses thereof
CN103788067A (en) * 2014-01-14 2014-05-14 北京万全德众医药生物技术有限公司 Preparation method of 3-[3-ethoxy-4-(N-phthaloyl)]phenylamino-N-[3-chloro-4-(2-pyridylmethoxyl]phenyl-2-cyano-2-acrylamide
CN105367552A (en) 2015-01-09 2016-03-02 苏州晶云药物科技有限公司 Novel crystal form of neratinib maleate and preparation method thereof
WO2018005418A1 (en) * 2016-06-27 2018-01-04 Pliva Hrvatska D.O.O. Solid state forms of neratinib and salts thereof
US10392399B2 (en) 2016-09-08 2019-08-27 Kala Pharmaceuticals, Inc. Crystalline forms of therapeutic compounds and uses thereof
US10253036B2 (en) 2016-09-08 2019-04-09 Kala Pharmaceuticals, Inc. Crystalline forms of therapeutic compounds and uses thereof
EP3509421A4 (en) 2016-09-08 2020-05-20 Kala Pharmaceuticals, Inc. Crystalline forms of therapeutic compounds and uses thereof
CN106905234B (en) * 2017-04-12 2019-04-23 淮海工学院 A method of the synthesis chloro- 6- amino -7- ethoxyquinoline of linatinib intermediate 3- cyano -4-
CN107501174A (en) * 2017-07-25 2017-12-22 广州大学 A kind of synthetic method of quinoline
CN110770231B (en) * 2017-10-18 2022-11-22 江苏恒瑞医药股份有限公司 Preparation method of tyrosine kinase inhibitor and intermediate thereof
CN108084085B (en) * 2017-12-28 2019-11-26 山东铂源药业有限公司 A kind of preparation method of N- (the chloro- 4- of 3- (2- pyridomethoxy) phenyl) -2- cyanoacetamide
CN110357854A (en) * 2018-03-26 2019-10-22 江苏创诺制药有限公司 A kind of preparation method of linatinib
CA3098428A1 (en) 2018-04-18 2019-10-24 Constellation Pharmaceuticals, Inc. Modulators of methyl modifying enzymes, compositions and uses thereof
CA3100977A1 (en) 2018-05-21 2019-11-28 Constellation Pharmaceuticals, Inc. Modulators of methyl modifying enzymes, compositions and uses thereof
CN110818619B (en) * 2019-12-13 2021-03-02 山东铂源药业有限公司 Synthetic method of N- (3-chloro-4- (2-pyridylmethoxy) phenyl) -2-cyanoacetamide
CN113336742B (en) * 2021-06-29 2022-05-10 山东金吉利新材料有限公司 Synthesis method of pyrroltinib maleate intermediate
CN114736154B (en) * 2022-03-15 2023-07-21 安庆朗坤药业有限公司 Process for preparing N- (3-chloro-4- (2-pyridylmethoxy) phenyl) -2-cyanoacetamide
CN115124452B (en) * 2022-05-26 2024-03-01 安庆朗坤药业有限公司 Preparation method of 2- (4-amino-2-ethoxyphenyl) isoindole-1, 3-dione

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6002008A (en) * 1997-04-03 1999-12-14 American Cyanamid Company Substituted 3-cyano quinolines
US20050043537A1 (en) * 2003-08-19 2005-02-24 Wyeth Holdings Corporation Process for preparation of 4-amino-3-quinolinecarbonitriles

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6297258B1 (en) * 1998-09-29 2001-10-02 American Cyanamid Company Substituted 3-cyanoquinolines
US6288082B1 (en) * 1998-09-29 2001-09-11 American Cyanamid Company Substituted 3-cyanoquinolines
UA77200C2 (en) * 2001-08-07 2006-11-15 Wyeth Corp Antineoplastic combination of cci-779 and bkb-569
MXPA04007495A (en) * 2002-02-05 2004-11-10 Wyeth Corp Process for the synthesis of n-acyl-2-amino-4-alkoxy-5-nitrobenzoic acids.
CL2004000016A1 (en) * 2003-01-21 2005-04-15 Wyeth Corp 4-AMINO-2-BUTENOYL CHLORIDE COMPOUND OR A PHARMACEUTICALLY ACCEPTABLE SALT OF THE SAME; PROCEDURE TO PREPARE SUCH COMPOUND, USEFUL AS INTERMEDIARY IN THE SYNTHESIS OF INHIBITING COMPOUNDS OF PROTEIN QUINASA TIROSINA.
SG149817A1 (en) * 2004-01-16 2009-02-27 Wyeth Corp Quinoline intermediates of receptor tyrosine kinase inhibitors and the synthesis thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6002008A (en) * 1997-04-03 1999-12-14 American Cyanamid Company Substituted 3-cyano quinolines
US20050043537A1 (en) * 2003-08-19 2005-02-24 Wyeth Holdings Corporation Process for preparation of 4-amino-3-quinolinecarbonitriles

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DESAI P R ET AL: "BROMINATION OF .BETA.-ARYLAMINO ( -CYANO- AND .ACETYL-) ACRYLOANILIDES", JOURNAL OF THE INSTITUTION OF CHEMISTS (INDIA), CALCUTTA,, IN, vol. 62, no. 4, July 1990 (1990-07-01), pages 173, XP008068397, ISSN: 0020-3254 *
E. B. KNOTT AND R. A. JEFFREYS: "The strucutre of the solid reaction product of anilines and ethyl orthoformate", JOURNAL OF ORGANIC CHEMISTRY, vol. 14, 1949, pages 879 - 886, XP002396497 *
J. VAMECQ, P. BAC, C. HERRENKNECHT, P. MAUROIS, P. DELCOURT AND J. P. STABLES: "Synthesis and anticonvulsant and neurotoxic properties of substituted N-phenyl derivatives of the phtalimide pharmacophore", JOURNAL OF THE MEDICINAL CHEMISTRY, vol. 43, 2000, pages 1311 - 1319, XP008065485 *
PRICE C C ET AL: "A SYNTHESIS OF SUBSTITUTED 4-AMINOQUINOLINES", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 68, August 1946 (1946-08-01), pages 1246 - 1250, XP002072256, ISSN: 0002-7863 *
V. D. DYACHENKO AND R. P. TKACHEV: "3-Amino-3-thiopropanamide in the synthesis of functionally substituted nicotinamides", RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, vol. 39, no. 8, 2003, pages 1174 - 1179, XP002396496 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2777675C2 (en) * 2017-10-18 2022-08-09 Цзянсу Хэнжуй Медисин Ко., Лтд. Method for production of tyrosine kinase inhibitor and its intermediate compound

Also Published As

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KR20080016600A (en) 2008-02-21
EP1883621A2 (en) 2008-02-06
AU2006249598A1 (en) 2006-11-30
JP2008542267A (en) 2008-11-27
CN101180269A (en) 2008-05-14
NO20075643L (en) 2008-02-21
US20060270669A1 (en) 2006-11-30
ZA200710163B (en) 2008-12-31
CR9508A (en) 2009-06-25
IL187303A0 (en) 2008-04-13
CA2608394A1 (en) 2006-11-30
BRPI0610144A2 (en) 2010-06-01
WO2006127205A2 (en) 2006-11-30
MX2007014773A (en) 2008-02-20
RU2007139544A (en) 2009-06-27

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